Outside of aesthetics, make sure you have cleaners, maintenance and turnaround worked out so you go in with a solid plan.

My contractor has gotten impatient waiting for him and has started taking matters into his own hands (he did the jack hammering of the floors which my plumber said had "complications" and would "take forever to get through"). 

I think your plan has merit. 

In smaller towns, this is usually a specific individual within the Planning Department. 

Good point, if you have plans to sell in the near future, could be better to wait.

Will you use the HELOC as a short-term bridge, or plan to hold it longer?

I plan to do a 1031 into a new investment property.

I don't think Im paying my bookeepeer an outrageous amount, although with economies of scale (I have one commercial insurance plan, commerical portfolio loan from a single bank, one bank account, etc) it probably doesn't take the Bookeeper 3x to do my books compared to yours. 

ie, wind damages the roof and that lets in rain that damages sheetrock, floors, furnishings,...   

A complete overhaul of the kitchen and bathrooms, including cabinets, countertops, LVP flooring, electrical and plumbing fixtures.